Listed by Daire Gibney • Barrett and Valley Associates Inc. Bought with Killington Pico Realty.
Off market sep 2023 for $340K
$411,048
Est. refi paymentEst. refi$2,305/mo
4
bd
•
2.5 ba
•
2,686
sq ft
183 Pleasant St, Chester, VT 05143
About this home
Searching for a classic Vermont farmhouse offering endless possibilities? You have just found it! Welcome to 183 Pleasant St. a quaint Victorian home in the vibrant town of Chester VT. Enter through a large mudroom, perfect for ski and board storage. The first floor boasts an eat-in kitchen with a new refrigerator, a pantry/laundry room combo recently updated, a formal dining room complete with a pellet stove for cozy winter dinners, a living room, and a bedroom with an ensuite half bath. Ascend the staircase in the formal entryway to the second floor to find three additional bedrooms, two full baths, two huge bonus rooms, and a walk-in closet/storage space. Continue down the back steps that bring you to the mudroom and enter the huge 1600 sq ft semi-finished two-story barn that is perfect for a workshop, artist studio, or storage OR finish the space for more living space, in-law suite, or rental property. Set on a flat. 55 acres at the edge of town, lawn care is a breeze and there is a newer stone firepit and tons of room for gardening or activities. Walk to the village green, the local swimming hole, and Chester schools. This location is also ideal for ski and board enthusiasts, close to Okemo and Magic (20 mins), Bromley (30 mins), Killington (40 mins), and Snow (50 mins). Did we mention fiber optic internet, allowing lightning-fast speed to work from home? This expansive home would be perfect for a primary residence, vacation home, or investment. Move-in ready!
Single-familyProperty Type
1880Year Built
0.54 acresLot Size
$153Est. Price/Sq.Ft.
2 car garageParking
Listed by Daire Gibney• Barrett and Valley Associates Inc.
You will be so happy in this properly restored and renovated 2686 sf 5 bedroom, 3 bath 1860s farmhouse with attached 1728 sf 2-story barn. Every effort has been made to preserve the original 'feel' and layout while improvements were made. The first floor has spacious mudroom, completely updated kitchen with all appliances negotiable; laundry room, living room, dining room, guest bedroom, foyer and half bathroom. Ascend the staircase with its 'cattail' Newell post to the second floor that has the 2 full bathrooms, another living/family room, and 4 more bedrooms including the Master with its walk-in closet, bathroom and private staircase communicating with the mudroom. Brand new high efficiency Buderus Boiler and hot water tank in 2017; enjoy significant wintertime solar benefit given numerous, large south facing windows. New electrical and wiring since our ownership eliminated dangerous knob-and-tube, added wall light switches and useful outlets, and created a laundry room from the original kitchen pantry. Entire exterior repaired and revival paint job completed in 2018. This house has the added value of being zoned 'Residential/Commercial'; ply any trade from home office or barn/garage shop! 3 blocks to shopping/dining. 1 mile to schools and town center. 2 major ski areas within 15 miles. Pleasant Street/Rte11 is a priority of snowplows.
PrimeMLS #4324800
Aug 18, 2014
Sold
$147,500
$55/sq ft
Nov 7, 2013
Listed
$179,000
$67/sq ft
HUGE PRICE REDUCTION! MUST SEE! Step into a Chester town classic. Enter into a beautiful foyer with large grand stair case. Over sized dining and living. Large mud area with separate entrance to a en suite or office space. Four large bedrooms. A beautiful barn that offers ample opportunity for antiques, workshop, storage, or even more living space. The kitchen is in need of your creative touch. Walk to town and all that Chester has to offer.
Year
Property tax
Land + Additions
Assessment*
2025
$4,175 (+4.8%)
$30,400 + $193,300
$223,700
2024
$3,985 (+16.2%)
$30,400 + $193,300
$223,700
2023
$3,429 (−34.1%)
$30,400 + $193,300
$223,700
2022
$5,204 (−1.4%)
$30,400 + $193,300
$223,700
2021
$5,278 (+5.8%)
$30,400 + $193,300
$223,700
2020
$4,990 (+36.4%)
$30,400 + $193,300
$223,700
2019
$3,658 (+0.7%)
$35,800 + $150,600
$186,400
2018
$3,634 (−0.3%)
$35,800 + $150,600
$186,400
2016
$3,643 (−2.9%)
$35,800 + $150,600
$186,400
2015
$3,751
$35,800 + $150,600
$186,400
2013
$35,800 + $247,400
$283,200
Tax history for 183 Pleasant St
Year
Property tax
Land + Additions
Assessment*
2025
$4,175 (+4.8%)
$30,400 + $193,300
$223,700
2024
$3,985 (+16.2%)
$30,400 + $193,300
$223,700
2023
$3,429 (−34.1%)
$30,400 + $193,300
$223,700
2022
$5,204 (−1.4%)
$30,400 + $193,300
$223,700
2021
$5,278 (+5.8%)
$30,400 + $193,300
$223,700
2020
$4,990 (+36.4%)
$30,400 + $193,300
$223,700
2019
$3,658 (+0.7%)
$35,800 + $150,600
$186,400
2018
$3,634 (−0.3%)
$35,800 + $150,600
$186,400
2016
$3,643 (−2.9%)
$35,800 + $150,600
$186,400
2015
$3,751
$35,800 + $150,600
$186,400
2013
$35,800 + $247,400
$283,200
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
4
Baths
2.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.54 Acres
Year renovated
—
Sq. Ft.
2,686
Year built
1880
Style
Single Family Residential
County
Windsor County
APN
14404510540
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 2, 2026.
Property details
Parking
Parking & Garage
Garage Capacity: 2
Location: Attached
Direct Entry, Finished, Heated, Storage Above, Barn